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Being an entrepreneur is a frightening experience. You’re
constantly faced with challenges that frequently put you on edge.

Over the past six years, I’ve been involved in three different
startups. Each offered unforgettable experiences -- most good,
depending on your outlook. It certainly hasn’t been easy to
co-found, lead or grow any of these businesses, and I’m lucky
I’ve worked with excellent teams throughout my career. Though I
haven’t yet seen it all, I’ve seen enough to realize the hard
reality that is starting a business.

Here is a (relatively) short list of things that easily kept me
up at night:

1. You’re replaceable. Your customers, strategic
partners, suppliers and teammates will always appreciate your
contributions, but there is always going to be someone that’s
better, smarter and nicer than you are. You have no time to be
complacent because the bar is set higher and higher each day for
individuals in your field. Also, no one has the patience to deal
with jerks. So stay hungry and never stop treating people well.
Do these things and you’ll be irreplaceable.

2. Reputation matters. Don’t become the person everyone loves to hate.
Instead, be the most outstanding person you can be. Do nothing
that compromises your integrity. Stay honorable. People will
like you more.

3. You’re responsible (even when it’s not your
fault). It’s true what they say. There’s absolutely no
“I” in team. If something breaks, it’s everyone’s job to fix it. It’s
unproductive to point fingers and no one benefits from
pettiness. Fix it, prevent the problem from recurring and move
on.

4. Others depend on you. It’s a scary thought
that you’re responsible to more people than just yourself. Your
customers trust you to keep them happy, your team members turn to
you for their livelihood and your investors expect return on
investment. Your actions and decisions impact them, so
remember to do what’s best for everyone -- not just you.

5. You’ll eventually have to disappoint people.
Some of your professional relationships will have to end. Some of
your customers may not always get what they want. You can no
longer grow if you’re carrying deadweight employees or fail to
fire abusive customers, so
trim the fat, but beware of leaving a bitter taste in their
mouths or you’ll face the consequences.

6. Too much of a good thing is actually truly
terrible. One day, you can be peddling your wares to
local shop owners, a dozen at a time. The next day, all of the
major news networks want to promote your product -- for
free. You gladly accept and receive more sales in 12
hours then you’ve received in the lifetime of your business.
Hooray! But wait, this gift has turned into a curse. As a startup, you
have to be prepared for the worst-case scenario.

7. You’re forgettable. Despite your
accomplishments and the noteworthy mentions of you garnered in
the press, within weeks, your business can feel like yesterday’s
news. To be competitive and relevant, you must continue to
innovate.

8. Building a business costs more than just
money. There’s also a price you pay when you make a
habit of pulling the graveyard shift evening after evening after
evening. Your relationships suffer and your happiness may
decline. It’s easy for your work to consume you -- just know that
you don’t have to let that happen.

9. Failure happens. It's difficult to stomach,
but failure is natural. What makes matters worse is that your
family and friends watch your every move anxiously hoping you’ll
succeed. You’re allowed to fail and should fold a
campaign or project if it no longer makes sense to continue
on. When you’re ready to start a new adventure, you’ll be more
prepared than ever.

10. Equity is messy. Fortunately, I’ve worked
with honest people who’ve sought to compensate me fairly. At the
same time, I’ve witnessed many not-so-lucky startup folk get
taken advantage of. Be sure to negotiate.

11. You’ll face rejection -- a lot of it. Be
prepared to hear 100 -- perhaps 300 -- “no’s” before you ever get
a resounding “yes” from someone. You may think it’s a numbers
game: the more people you ask, the closer you get to finding
your first customer. The real secret isn’t trying to sell more
people though. It’s selling your idea, product or service to
the right people, improving your pitch, story and salesmanship
each time.

I’m only six years and three startups into my career and I, most
certainly, have many more lessons I need to learn. Ultimately,
it’s these lessons that help you become a better entrepreneur.